In September, the summer crowds disperse, the sun's intensity wanes, and it's a fantastic time to visit Annapolis and the Chesapeake Bay region. Enjoy historical sites and museums, crowd-free shopping and dining, and outdoor activities-whether hiking a trail at one of the area's parks or paddling on the water. Also, consider taking in the Maryland Renaissance Festival in Crownsville. With this 22-acre fictional 16-century English village with over 200 performers, ten stages, a 5,000-seat jousting arena, 148 craft shops and 48 food/beverage facilities, it's Maryland's premier outdoor event.

First Sunday Arts Festival
When: Sunday, September 1st (and every first Sunday through November 3rd) 11:00 a.m. to 5:00 p.m.
Where: First block of West and Calvert Streets, Annapolis
Admission: Free

Enjoy live entertainment and the works of 100 local and regional artists as you stroll along the first block of West Street and Calvert Street next to Whitmore parking garage. Local restaurants set up outside cafes that are perfect for people watching and an afternoon bite to eat. Free parking for the family-friendly event is available at the state parking garage on the corner of Calvert and Bladen Streets. Visit for more information.

43rd Annual Maryland Renaissance Festival
When: Weekends and Labor Day, August 24th through October 20th; 10:00 a.m. – 7:00 p.m. rain or shine
Where: 1821 Crownsville Road, Annapolis

The largest even of its kind in eastern North America and the second largest Renaissance Festival in the Country is celebrating its 43rd season at Revel Grove. Travel back in time as you immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court. The festival includes 250+ entertainers, including jugglers, magicians, musicians, comedians, artists and more, ten stages, a 3,000 seat jousting arena, 130 craft shops, 42 food and beverage emporiums, games, attractions - all on a 25-acre site that includes 80 acres of complimentary parking. Let merriment abound! Visit for more information.

52nd Annual Maryland Seafood Festival
When: Saturday-Sunday, September 7th-8th, 2019; Saturday, 10:00 a.m. to 9:00 p.m.; Sunday, 10:00 a.m. to 7:00 p.m.
Where: Sandy Point State Park, 1100 East College Parkway, Annapolis
Admission: Adults, $15; kids 12 and under, free.

Enjoy seafood dishes, interactive cooking demonstrations by notable area chefs, the famous crab soup cook-off, competitions, kids' rides and activities, live entertainment and more. Enjoy a relaxing day along the shores of the scenic Chesapeake Bay. Proceeds benefit local nonprofit organizations. Visit for more information.

Maryland Seafood Festival

Anne Arundel County Fair
When: Wednesday - Sunday, September 11th - 15th, 2019
Where: Anne Arundel County Fairgrounds, 1450 Generals Highway, Crownsville

For nearly 65 years, the Anne Arundel County Fair has been amusing visitors of all ages with fun contests including hog calling and watermelon eating! Booths feature everything from homemade wine and home-brewed beer to furniture and one-of-a-kind Christmas decorations. Kids will enjoy the amusement rides, illusionist show, 4H Club animals and interactive car racing. There’s something for everyone! Visit for more information.

Anne Arundel County Fair

Blazers, Bourbon, Cigars
When: Thursday, September 26th, 2019; 6:00 p.m. to 9:00 p.m.
Where: William Paca House and Garden, 186 Prince George Street
Admission: $100-$150

Enjoy an action-packed night of bourbon tastings, fine cigars, wonderful food, and networking with the “Who’s Who” of Annapolis gentlemen. Gentlemen already well-versed in the art of drawing subtle flavors out of a glass of aged whiskey and those just wanting to learn more will enjoy this unique evening featuring more than a dozen varieties of bourbon. VIPs enjoy early admission at 5:00 p.m. for a private tasting hosted by a master Maker’s Mark specialist, John Vicker-Smith II. He’ll describe current trends in bourbon while leading a deep sensory dive into the rich flavor profiles of different bourbons. VIP guests will enjoy all-you-can-taste bourbon with a special memento to take home, an exclusive Maker’s Mark cigar, and other surprises. Sponsored by: Maker’s Mark. Visit for more information.

Annual Boatyard Beach Bash
When: Saturday, September 14th, 2019; 5:00 p.m. to 10:00 p.m.
Where: Annapolis Maritime Museum, 723 Second Street, Annapolis
Admission: General admission, $85 – includes dinner and 2 beverage vouchers; VIP (Very Important Parrotheads), $150 – ticket holders get to mingle with the band members and enjoy all the benefits of general admission.

Event founding sponsor, Boatyard Bar and Grill, has put together a star-studded lineup that includes original members of Jimmy Buffett’s Coral Reefers band performing on a waterfront stage. In 2017, Peter Mayer, Brendan Mayer and Doyle Grisham – as well as world-class musicians, John Frinzi, Scott Kirby, Aaron Scherz and Sunny Jim, along with James White and JD Spradlin from Radio Margaritaville, entertained throughout the evening. Evening includes an extensive grilled buffet dinner and cocktails. Proceeds benefit the Annapolis Maritime Museum’s children’s education efforts.

Greenstreet Gardens Fall Festival
When: September 21st, 2019 - October 27th, 2019; 10:30 a.m. to 5:00 p.m.
Where: Greenstreet Gardens, 391 West Bay Front Road, Lothian, MD 20711

Six weekends of fall festivities is back and even better than before! Come enjoy different themed events and activities each weekend with family and friends. Our 5-acre corn maze, pumpkin bowling, jumping pillow, haunted hay ride, cow train, giant teepee, corn box, straw castle, underground slide and more - is everything you could ever imagine!

MD Ave/State Circle Fall Festival

Dinner Under the Stars
When: Every Wednesday evening, through September 18th, 2019.
Where: The first block of West Street in downtown Annapolis
Admission: Making reservations ahead of time is highly recommended. 

The first block of West Street (from Church Circle to Calvert Street), located in the heart of the Arts District, will be closed to traffic on Wednesday evenings and filled with café tables reminiscent of the open air cafés in France, Spain, and Italy. Live music and special art exhibits will appear all over West Street, adding to the ambiance as you dine beneath a canopy of lights. 

Homestead Gardens Annual Fall Festival
When: Every weekend, September 21st - October 27th; 11:00 am - 5:00 pm
Where: Homestead Gardens, 743 West Central Avenue, Davidsonville
Admission: $12, kids 3 and under free

Celebrate autumn at this family-friendly festival that takes place on 30 acres surrounding Homestead's showroom. It features more than 20 activties, rides and attractions, including hayrides, pipe slide, corn cannon, pony rides, pumpkin express and more. Meet birds of prey up close and personally watch an expert carve a pumpkin. Wristband includes free parking, live music, attractions and rides. Pumpkins and food available for purchase. To learn more, visit

Homestead Gardens Fall Festival

Historic Hauntings Tours
When: Fridays & Saturdays in October 
Where: Tours depart from the Historic Annapolis Museum Store, 99 Main Street, Annapolis Admission: Adults, $23; Children ages 3-11, $13; Children 2 and under, free

Join Watermark for a Historic Ghost Walk of downtown Annapolis. Hear about unexplained footsteps, the Gravedigger and the poor souls that were hanged to save room in local jails. As the sun sets and darkness descends, a spirited period dressed guide will lead you by candlelight through the historic, haunted street of Annapolis. You'll hear stories - all of which are based on facts - of the spirits who dwell in the 18th century buildings and linger in the mist. It will give you a whole new perspective on Maryland's capital city. Suitable for all ages. Presented by Historic Annapolis Foundation and Watermark Journeys. Visit for more information.

30th Annual Kunta Kinte Heritage Festival
When: September 28th, 10:00 am – 7:00 pm
Where: Susan Campbell Park - Dock St, Annapolis
Admission: Free (Donations are greatly appreciated)

Enjoy the rich heritage of Kunta Kinte whose story from the Gambia to Annapolis and for generations on down was told in the book Roots: Saga of an American Family by Alex Haley.  A family-friendly cultural festival celebrating the history and Heritage of people of African American, African, and Caribbean descent. This is the 29th year of this celebration that includes a full day of live music, dance, ethnic foods and wares for sale. You can discover a full list of events and activities HERE.

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Additional September Links

  • Renaissance Festival

    Renaissance Festival

    One of Maryland's most anticipated events of the summer, the Renaissance Festival has a little something for everyone in the family.

    Learn more